MXPA06004296A - Low-viscosity oligocarbonate polyols - Google Patents
Low-viscosity oligocarbonate polyolsInfo
- Publication number
- MXPA06004296A MXPA06004296A MXPA/A/2006/004296A MXPA06004296A MXPA06004296A MX PA06004296 A MXPA06004296 A MX PA06004296A MX PA06004296 A MXPA06004296 A MX PA06004296A MX PA06004296 A MXPA06004296 A MX PA06004296A
- Authority
- MX
- Mexico
- Prior art keywords
- aliphatic
- formula
- integer
- polyols
- preparation
- Prior art date
Links
- 229920005862 polyol Polymers 0.000 title claims abstract description 32
- 150000003077 polyols Chemical class 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 26
- -1 aliphatic polyol Chemical class 0.000 claims abstract description 22
- 150000002009 diols Chemical class 0.000 claims abstract description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- IEJIGPNLZYLLBP-UHFFFAOYSA-N Dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229910052757 nitrogen Chemical group 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 238000005809 transesterification reaction Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 4
- ROORDVPLFPIABK-UHFFFAOYSA-N Diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive Effects 0.000 claims description 4
- 150000005677 organic carbonates Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 125000005842 heteroatoms Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229920001228 Polyisocyanate Polymers 0.000 description 13
- 239000005056 polyisocyanate Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- POILWHVDKZOXJZ-ARJAWSKDSA-M (Z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 10
- 239000011572 manganese Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 101700000038 mpas Proteins 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011527 polyurethane coating Substances 0.000 description 7
- 239000010936 titanium Substances 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N Isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052769 Ytterbium Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N 1,6-Hexanediol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- LMCBEWMQFKWHGU-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O LMCBEWMQFKWHGU-UHFFFAOYSA-N 0.000 description 4
- 238000009423 ventilation Methods 0.000 description 4
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N Cyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 239000002981 blocking agent Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
- 230000005593 dissociations Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000010422 painting Methods 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-Butanediol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N DABCO Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- UAOMVDZJSHZZME-UHFFFAOYSA-N Diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N Diphenylmethane p,p'-diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000000240 adjuvant Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000000903 blocking Effects 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium monoxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 230000000873 masking Effects 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- AWSFICBXMUKWSK-UHFFFAOYSA-N ytterbium(3+) Chemical compound [Yb+3] AWSFICBXMUKWSK-UHFFFAOYSA-N 0.000 description 2
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 1
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-Propanediol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- AGJCSCSSMFRMFQ-UHFFFAOYSA-N 1,4-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=C(C(C)(C)N=C=O)C=C1 AGJCSCSSMFRMFQ-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N 1,5-Pentanediol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- OUJCKESIGPLCRN-UHFFFAOYSA-N 1,5-diisocyanato-2,2-dimethylpentane Chemical compound O=C=NCC(C)(C)CCCN=C=O OUJCKESIGPLCRN-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 description 1
- IBAJWKQKPIIFQU-UHFFFAOYSA-N 2-methoxypropan-2-ylcyclohexane Chemical compound COC(C)(C)C1CCCCC1 IBAJWKQKPIIFQU-UHFFFAOYSA-N 0.000 description 1
- ZDKYYMRLZONTFK-UHFFFAOYSA-N 3,4-bis(isocyanatomethyl)bicyclo[2.2.1]heptane Chemical compound C1CC2(CN=C=O)C(CN=C=O)CC1C2 ZDKYYMRLZONTFK-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1H-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N Etohexadiol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N Hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-SNAWJCMRSA-N Methylethyl ketone oxime Chemical compound CC\C(C)=N\O WHIVNJATOVLWBW-SNAWJCMRSA-N 0.000 description 1
- BXAQFTLBYMGEIQ-UHFFFAOYSA-N N,N-dimethylhexan-3-amine Chemical compound CCCC(CC)N(C)C BXAQFTLBYMGEIQ-UHFFFAOYSA-N 0.000 description 1
- DLSOILHAKCBARI-UHFFFAOYSA-N N-benzyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NCC1=CC=CC=C1 DLSOILHAKCBARI-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial Effects 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical class N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- YRPWLKVCRKAUAO-UHFFFAOYSA-N bismuthonium Chemical compound [BiH4+] YRPWLKVCRKAUAO-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N butylene glycol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 150000004653 carbonic acids Chemical class 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-M dibutyl phosphate Chemical compound CCCCOP([O-])(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-M 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- AGAYZDNGCFSGLT-UHFFFAOYSA-N diphenylmethane monoisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1 AGAYZDNGCFSGLT-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- DUDXQIXWPJMPRQ-UHFFFAOYSA-N isocyanatomethylcyclohexane Chemical compound O=C=NCC1CCCCC1 DUDXQIXWPJMPRQ-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000000576 supplementary Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-M urea-1-carboxylate Chemical compound NC(=O)NC([O-])=O AVWRKZWQTYIKIY-UHFFFAOYSA-M 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Abstract
TThe present invention relates to low-viscosity oligocarbonate polyols, the ir preparation and use. The oligocarbonate polyols are based on diols of formul a I below, which are used in combination with a further aliphatic polyol.
Description
OLIGOCARBONTHE LOW VISCOSITYOPOLIOLS
Field of the Invention The present invention relates to low viscosity oligocarbonatopolols, their preparation and use. BACKGROUND OF THE INVENTION Oligocarbonatopolols are important pre-products, for example in the manufacture of plastics, paints and adhesives. These are reacted, for example, with isocyanates, epoxides, (cyclic) esters, acids or acid anhydrides (DE-A 1995902). They can be manufactured mainly from aliphatic polyols by reaction with phosgene (for example, DE-A 1595446), esters of bis-chlorocarbonic acid (for example, DE-A 857948), diaryl carbonates (for example, DE document). -A 1012557), cyclic carbonates (for example, DE-A 2523352) or dialkyl carbonates (for example, WO 2003/2630). The oligocarbonatopolioles described in the state of the art with a number average molecular weight (Mn) of 500 to 5000 g / mol are characterized because they occur at room temperature (23 ° C) in a state of solid aggregation or in a state of aggregation viscous liquid. In this respect the viscosity range of liquid oligocarbonatopolyoles at room temperature ranges according to each composition and weight REF: 171370 molecular number average from 2500 mPas to 150000 mPas. In this respect viscosities of < 3500 mPas only by oligocarbonatopolols which often have, in addition to carbonate structures, also ester units and / or number average molecular weights = 1000 g / mol. However, this leads in the case of the presence of ester units to which, for example, in polyurethane systems based on the so-called polyestercarbonatopolols, the stability against hydrolysis is negatively influenced in comparison with systems based on pure oligocarbonatopolols. . The same is valid for the case of the use of oligocarbonatopolioles containing ether with regard to the worst stability against UV radiation against a system based on pure oligocarbonatopolioles. One more possibility to prepare pure low viscosity oligocarbonatopolols consists of the use of hydroxyalkyl-terminated silicones. The main preparation of those oligocarbonatodiols having exclusively hydroxyalkyl-terminated silicone compounds as the diol component is already known and is described in Chem. Ber. (1966), 99 (2), 1368 to 1383. However, in the phosgenation preparation mentioned there is no indication that the oligomers or polymers obtained exclusively contain hydroxy-functional end groups. It is further shown that such oligocarbonate diols based only on hydroxyalkyl-terminated silicone compounds are not suitable for the preparation of polyurethane coatings, since these present to a large extent incompatibilities with (poly) isocyanates. Furthermore, EP-A 1035153 shows, for example, the preparation of polysiloxanes modified with polyester polyols containing carbonate groups. In this regard, these are hydroxyalkyl-terminated silicones, which were reacted with polyester polyols and esters of organic carbonic acids to give copolymers. Copolymers of this type, on whose viscosities no detailed data were given, present in relation to their stability against hydrolysis due to the presence of ester groups a negative behavior similar to that of the other polyestercarbonatopolols described above, so that these copolymers in Most cases are only for use as additives in coatings. Nothing is disclosed as to carbonates free of carboxylic acid ester groups. Detailed Description of the Invention Therefore, it was an object of the present invention to provide oligocarbonatopolols having at room temperature (23 ° C) a viscosity measured according to DIN EN ISO 3219 and depending on a number average molecular weight between 500 and 10000 g / mol less than 15,000 mPas and that does not present the previously indicated drawbacks. It was found that oligocarbonatopolols containing structural units derived from a diol of formula (I), achieve the objective on which the invention is based.
wherein n is an integer from 1 to 50, m is an integer from 1 to 20, Ri, R2 are independently from each other an alkyl moiety Ci to C20, which may be linear, cyclic or branched and optionally it is unsaturated, and (X) m is a group containing carbon with 1 to 20 C atoms, whose chain can also be interrupted with heteroatoms such as oxygen, sulfur or nitrogen. The subject of the invention are therefore aliphatic oligocarbonatopolols with a number-average molecular weight (Mn) of 500 to 10000 g / mol, which consist of a polyol component, containing from 1 to 99 mol% based on this polyol component of diols of formula (I) and also has as constituent at least one further aliphatic polyol, totaling the sum of the amounts of the diol of formula (I) and of the other polyols contained in 100% by moles. It is preferred in formula (I) that (X) m is an alkyl group, n is an integer from 1 to 20, particularly preferably from 1 to 10, m is an integer from 1 to 10, with particular preference from 1 to 5, and Ri, R2 are methyl, ethyl or propyl, especially preferably Rx = R2 = methyl. Preferred are diols of formula (I) which contain in the aliphatic polyol component from 1 to 90% by mol, particularly preferably from 1 to 75% by mol. The preparation of the hydroxyalkyl-terminated silicone compounds represented in the formula (I) is known and described, for example, in Chemie und Technologie der Silicone, second edition, 1968, Chemie Verlag, Weinheim, Germany. A further object of the invention is the preparation of oligocarbonatopolols according to the invention as well as coatings, adhesives and sealing substances as well as polyurethane pre-polymers, which are based on the oligocarbonatopolols according to the invention. Preferred are polyurethane-containing coatings, in which the oligocarbonatopolols according to the invention are used as a reactive component against (poly) isocyanates.
The preparation of the oligocarbonatopolols according to the invention can be carried out according to a process described in the state of the art, such as, for example, phosgenation or transesterification. Preferably, the oligocarbonatopolols according to the invention are prepared by transesterification of organic carbonates, such as, for example, aryl, alkyl or alkylene carbonates, which are known for their simple preparation and good availability, with a polyol component. Examples are diphenyl carbonate (DPC), dimethyl carbonate (DMC), diethyl carbonate (DEC), ethylene carbonate, etc. In addition to the diols according to formula (I), aliphatic alcohols with 2 to 100 C atoms and OH = 2 functionality are used in the polyol component. These alcohols may be linear, cyclic, branched, unbranched, saturated or unsaturated and the OH functions may be attached to primary, secondary or tertiary C atoms. Examples are: ethylene glycol, 1,3-propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2-ethylhexanediol, 3-methyl-1, 5-pentanediol, cyclohexanedimethanol, trimethylolpropane, pentaerythritol, dimerdiol, sorbitol. In addition, discrete mixtures of the above-mentioned aliphatic polyols together with the compounds of formula (I) can also be present in the polyol components used for the transesterification. Preferred aliphatic polyols are aliphatic or saturated cycloaliphatic polyols, which optionally are branched and have primary or secondary attached OH groups and an OH = 2 functionality. For the acceleration of the transesterification of the organic carbonates with the polyols used in accordance with The invention can be used mainly all transesterification catalysts known from the state of the art. Both soluble catalysts (homogeneous catalysis) and also heterogeneous transesterification catalysts are possible in this respect. Hydroxides are particularly suitable for the preparation of the oligocarbonatopolols according to the invention, oxides, metal alcoholates, carbonates and organometallic compounds of the groups la, lia, Illa and IVa of the periodic system of elements according to Mendelejew, of groups IIIb and IVb as well as the elements and compounds of the group of rare earth metals, especially the compounds of titanium, zirconium, lead, tin, antimony, yttrium and ytterbium.
They are to be mentioned, for example: LiOH, Li2C03, K2C03, CaO,
Ti (OiPr) 4, Ti (OiBu) 4, Zr (0iPr) 4, tin octoate, dibutyltin dilaurate, bis-tributyltin oxide, tin oxalate, lead stearate, Sb03, yttrium acetylacetonate (III), acetylacetonate of Ytterbium (III). Preference is given to using titanium and / or zirconium alcoholate compounds, for example Ti (01Pr) 4, Ti (01Bu) 4, Zr (01Pr) 4, organic tin compounds such as dibutyltin dilaurate, bistributyltin oxide, dibutyltin oxide , as well as acetylacetonate compounds of rare earth metals such as yttrium acetylacetonate (III) and / or ytterbium acetylacetonate (III). Yttrium acetylacetonate (III), ytterbium (III) acetylacetonate and / or titanium tetraisopropylate are very particularly preferred. The catalyst content is from 1 to 1000 ppm, preferably from 1 to 500 ppm, particularly preferably from 1 to 250 ppm, based on the amount of the oligocarbonate according to the invention. The catalyst can be left in the product, separated, neutralized and / or masked after the completion of the reaction. Preferably the catalyst is left in the product. In the case of a masking, phosphoric acids and their derivatives are preferably used, such as, for example, H3P04, dibutyl phosphate, etc. as a masking agent. For the preparation of polyurethane coatings based on oligocarbonatopolols according to the invention, all (poly) isocyanates known from the state of the art can be used as reactive components against hydroxyl groups. The polyisocyanates reactive with hydroxyl groups are discretional polyisocyanates, consisting of at least two diisocyanates prepared by modification of aliphatic, cycloaliphatic, araliphatic and / or simple aromatic diisocyanates, with structure of uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazintrione, as described, for example, in J. Prakt. Chem. 336 (1994) 185 to 200, DE-A 1670666, 1954093, 2414413, 2452532, 2641380, 3700209, 3900053 and 3928503 or EP-A 336205, 339396 and 798299. Suitable diisocyanates for the preparation of such polyisocyanates they are discretionary diisocyanates which can be obtained by phosgenation or by processes without phosgene, for example by thermal urethane cleavage, with a molecular weight range of 140 to 400 with isocyanate groups linked aliphatically, cycloaliphatically, araliphatically and / or aromatically, for example, 1,4-diisocyanatobutane, 1,6-diisocyanatohexane (HDI), 2-methyl-l, 5-diisocyanatopentane, 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4- or 2,4-trimethyl -1,6-diisocyanatohexane, 1, 10-diisocyanatodecane, 1,3- and 1,4-diisocyanatocyclohexane, 1,3- and 1,4-bis- (isocyanatomethyl) -cciohexane, 1-isocyanato-3, 3, 5 -trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), 4,4'-diisocyanatodicyclohexylmethane, 1-isocyanate-1 -methyl- 4 (3) isocyanato-methylcyclohexane, bis- (isocyanatomethyl) -norbornane, 1,3- and 1,4-bis- (2-isocyanato-prop-2-yl) -benzene (TMXDI), 2,4 and 2, 6-diisocyanatotoluene (TDl), 2,4'- and 4,4'-diisocyanatodiphenylmethane (MDl), 1,5-diisocyanatophthalene or discretional mixtures of such diisocyanates. As regards polyisocyanates or mixtures of polyisocyanates, it is preferably of the type mentioned with isocyanate groups exclusively bonded aliphatically and / or cycloaliphatically. Polyisocyanates or mixtures of polyisocyanates with an isocyanurate structure based on HDI, IPDI and / or 4,4'-diisocyanatodicyclohexylmethane are particularly preferred. Furthermore, it is also possible to use said blocked polyisocyanates and / or isocyanates, preferably polyisocyanates or mixtures of blocked polyisocyanates, very particularly preferably polyisocyanates or mixtures of blocked polyisocyanates with isocyanurate structure based on HDI, IPDI and / or 4,4'-diisocyanatodicyclohexylmethane. The blocking of (poly) isocyanates for the temporary protection of the isocyanate groups is a work procedure which has been known for a long time and is describedFor example, in Houben Weyl, Methoden der organischen Chemie XIV / 2, pages 61 to 70. As blocking agents are, for example, all compounds that can be cleaved by heating the (poly) isocyanate blocked optionally in presence of a catalyst. Suitable blocking agents are, for example, sterically hindered amines as dicyclohexylamine, diisopropylamine, N-tert-butyl-N-benzylamine, caprolactam, butanone oxime, imidazoles with different substitution patterns that may arise, pyrazoles such as 3,5-dimethylpyrazole , triazoles and tetrazoles, likewise alcohols such as isopropanol, ethanol. In addition, there is also the possibility of blocking the isocyanate groups, so that the blocking agent is not cleaved in an additional reaction, but the intermediate phase formed between them is reacted. This is especially the case in the cyclopentanon-2-carboxyethyl ester, which reacts in the thermal crosslinking reaction completely in the polymeric lattice and is not cleaved again. As catalysts for the reaction of the oligocarbonate polyols according to the invention and component (poly) -isocianato above described catalysts can be used as commercial organometallic compounds of the elements aluminum, tin, zinc, titanium, manganese, iron, bismuth or zirconium also as, for example, dibutyltin dilaurate, zinc octoate, titanium tetraisopropylate. In addition, tertiary amines, such as, for example, 1,4-diazabicyclo [2.2.2] octane, are also suitable.
It is also possible to accelerate the reaction of the oligocarbonatopolols according to the invention with the (poly) isocyanate components, carrying out this at temperatures between 20 and 200 ° C, preferably between 40 and 180 ° C. In addition to the exclusive use of the Oligocarbonatopolols according to the invention can also be used mixtures of the oligocarbonatopolols according to the invention and other compounds reactive with (poly) isocyanate, such as, for example, polyether polyols, polyester polyols, polyacrylate polyols, polyamines, aspartates, etc. The ratio of (poly) isocyanate component to component which is reactive towards the isocyanate group is dimensioned in this respect so as to result in a ratio of free NCO groups and, where appropriate, blocked relative to those of reactive component to the isocyanate group of 0.3 to 2, preferably 0.4 to 1.5, particularly preferably 0.5 to 1.2. Additionally, the polyurethane coatings according to the invention may contain adjuvants customary in coating technology, such as inorganic or organic pigments, other organic photoresists, radical scavengers, paint additives, as dispersants, leveling agents, thickeners, defoamers. and other adjuvants, adhesives, fungicides, bactericides, stabilizers or inhibitors and other catalysts. Such coating agents according to the invention can be used, for example, in the fields of plastic painting, automotive interior / exterior painting, floor covering, balconies and / or wood painting / furniture. Examples The determination of the hydroxyl number (IOH) was carried out according to DIN 53240-2. The number average molecular weight (Mn) was calculated from the ratio known by the person skilled in the art between the hydroxyl number and the theoretical hydroxyl functionality. The determination of the viscosity was carried out using a rotational viscometer "RotoVisco 1" from the company Haake, Germany according to DIN EN ISO 3219. If not stated otherwise, the temperature data given in the following examples refer respectively to the Boiler temperature of the reaction mixture. EXAMPLE 1 Preparation of an oligocarbonatopolol according to the invention In a three-necked 1 1 flask with stirrer and reflux condenser, 139.5 g (75% by mole) of 1,6-hexanediol and 223.0 g ( 25 mole%) of Baysilone® OF / OH 502 at 6% (GE-Bayer Silicones, Germany) under a nitrogen atmosphere and dehydrated at 110 ° C and 2 KPa of pressure for 2 hours. As for Baysilone® OF / OH 502 at 6%, it is a polydimethylsiloxane with hydroxyalkyl (a, β-carbinol) functionality. Then it was vented with nitrogen and 0.008 g of titanium tetraisopropylate as well as 194.7 g of dimethyl carbonate were added and the reaction mixture was maintained for 24 hours under reflux (oil bath temperature 110 ° C). The reflux condenser was then replaced by a Claisen bridge and the dissociation product generated by methanol and the dimethyl carbonate still present were distilled off. For this, the temperature of 110 ° C was increased in the period of 2 hours to 150 ° C and after reaching. the temperature was maintained for 4 hours. After that, the temperature was then increased in the period of 2 hours to 180 ° C and after reaching it was maintained for another 4 hours. The reaction mixture was then cooled to 100 ° C and a stream of nitrogen (2 1 / h) was introduced into the reaction mixture. In addition, the pressure was reduced stepwise to 2 PKa, so that the head temperature did not rise above 60 ° C during the subsequent distillation. After reaching 2 PKa, the temperature was increased to 130 ° C and remained there for 6 hours. After ventilating and cooling, a liquid oligocarbonate diol was obtained at room temperature with the following characteristic data: hydroxyl number (IOH): 36, 9 mg KOH / g Viscosity at 23 ° C, D: 16: 1450 mPas Number average molecular weight (Mn): 3035 g / mol Comparative example 1 Preparation of a liquid oligocarbonate ester at room temperature In a three-neck flask of 2 1 with stirrer and reflux condenser 461.4 g (50 mole%) of 1,6-hexanediol were placed under a nitrogen atmosphere and dehydrated at 110 ° C and 2 PKa pressure for 2 hours. Then it was vented with nitrogen and 0.08 g of titanium isopropylate as well as 446.6 g (50% by mole) of e-caprolactone were added at 60 ° C, heated to 80 ° C and held there for
2 hours. Then 482.4 g of dimethyl carbonate was added and the reaction mixture was maintained for 24 hours under reflux
(Oil bath temperature 110 ° C). The reflux condenser was then replaced by a Claisen bridge and the dissociation product generated by methanol and the dimethyl carbonate still present were distilled off. For this, the temperature of 110 ° C was increased in the period of 2 hours to 150 ° C and after reaching the temperature it was maintained for 4 hours. After that, the temperature was then increased in the period of 2 hours to 180 ° C and after reaching it was maintained for another 4 hours. The reaction mixture was then cooled to 100 ° C and a stream of nitrogen (2 1 / h) was introduced into the reaction mixture. In addition, the pressure was reduced stepwise to 2 PKa, so that the head temperature did not rise above 60 ° C during the subsequent distillation. After reaching 2 PKa, the temperature was increased to 180 ° C and remained there for 6 hours. After ventilating and cooling, a liquid oligocarbonate diol was obtained at room temperature with the following characteristic data: hydroxyl number (IOH): 34.8 mg KOH / g Viscosity at 23 ° C, D: 16: 78300 mPas Numerical number average molecular weight ( Mn): 3218 g / mol Comparative Example 2 Preparation of a liquid oligocarbonate etherpolyol at room temperature In a three-neck flask of 5 1 with stirrer and reflux condenser, 2788.6 g (100% by mole) of poly-THF® were placed. 250 (BASF AG, Germany) under a nitrogen atmosphere and dehydrated at 110 ° C and 2 PKa pressure for 2 hours. Then it was vented with nitrogen and 0.6 g of ytterbium acetylacetonate (III) as well as 1098.5 g of dimethyl carbonate were added and the reaction mixture was maintained for 24 hours at reflux (oil bath temperature 110 ° C. ). The reflux condenser was then replaced by a Claisen bridge and the dissociation product generated by methanol and the dimethyl carbonate still present were distilled off. For this, the temperature of 110 ° C was increased in the period of 2 hours to 150 ° C and after reaching the temperature it was maintained for 4 hours. After that, the temperature was then increased in the period of 2 hours to 180 ° C and after reaching it was maintained for another 4 hours. The reaction mixture was then cooled to 130 ° C and a stream of nitrogen (2 l / h) was introduced into the reaction mixture. In addition, the pressure was reduced stepwise to 2 PKa, so that the head temperature did not rise above 60 ° C during the subsequent distillation. After reaching 2 PKa, the temperature was increased to 180 ° C and remained there for 6 hours. After ventilation and cooling, a liquid oligocarbonate diol was obtained at room temperature with the following characteristic data: hydroxyl number (IOH): 35.4 mg KOH / g Viscosity at 23 ° C, D: 16: 17800 mPas Numerical average molecular weight ( Mn): 3160 g / mol Comparative example 3 Preparation of a pure oligocarbonatopoliol The procedure is the same as in comparative example 2 except that 2149.6 g (100% by mole) of the poly-THF® 250 were used instead. 1, 6-hexanediol as well as 2340.6 g of dimethyl carbonate and 0.52 g of ytterbium acetylacetonate (III) as starting materials. After ventilation and cooling, a waxy type oligocarbonate diol was obtained at room temperature with the following characteristic data: hydroxyl number (IOH): 39.8 mg KOH / g Viscosity at 23 ° C, D: 16: not determinable, since is a waxy solid. Number average molecular weight (Mn): 2800 g / mol Comparative example 4 Preparation of a liquid, pure oligocarbonatopoliol The same procedure was carried out as in comparative example 2, except that they were used instead of poly-THF® 250 1909 , 8 g (100% by mole) of 3-methyl-1,5-pentanediol as well as 2027.8 g of dimethyl carbonate and 0.46 g of ytterbium acetylacetonate (III) as starting materials. After ventilation and cooling, a viscous oligocarbonate diol was obtained at room temperature with the following characteristic data: hydroxyl number (IOH): 56, 2 mg KOH / g Viscosity at 23 ° C, D: 16: 72000 mPas Number average molecular weight (Mn): 2000 g / mol Comparative example 5 Preparation of a low viscosity, pure, oligocarbonatopoliol The same procedure as in the example Comparative 2 with the difference that 251.8 g (100% by mole) of Baysilone® OF / OH 502 at 6% was used in place of poly-THF® 250 (GE-Bayer) in a 1 1-necked flask. Silicones, Germany) as well as 42.5 g of dimethyl carbonate and 0.05 g of ytterbium acetylacetonate (III) as starting materials. After ventilation and cooling, a low viscosity oligocarbonate diol was obtained, liquid at room temperature with the following characteristic data: hydroxyl number (IOH): 58.5 mg KOH / g Viscosity at 23 ° C, D: 16: 17 mPas Weight molecular average molecular weight (Mn): 1900 g / mol Example 2: Preparation of a polyurethane coating according to the invention The oligocarbonate diol according to the invention prepared in Example 1 was mixed with Desmodur® Z 4470 (polyisocyanate based on IPDI, Bayer MaterialScience AG, Leverkusen, Germany) in the ratio of equivalents 1: 1.1 with supplementary addition of 50 ppm of dibutyltin dilaurate in a beaker and then the homogeneous mixture was applied on a glass plate by means of a doctor blade. The coating was then hardened for 30 minutes at 140 ° C. A clear, high-clear polyurethane film was obtained. Comparative example 6; Preparation of a polyurethane coating The procedure was the same as in Example 2 except that the preparation was used as comparative example 5 as oligocarbonate diol. The mixture obtained was turbid and showed phase separation. The preparation of a polyurethane coating was not possible. As can be seen from the comparison of Example 1 with Comparative Examples 1 to 4, the oligocarbonatopoliol according to the invention has a viscosity clearly inferior to equal or even higher molecular weight, without implying the drawbacks of an ester or ether structure. Furthermore, the comparison of example 2 and comparative example 6 shows that only polyurethanes or polyurethane coatings can be prepared with the oligocarbonatopolyol according to the invention. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.
Claims (3)
- Having described the invention as above, the content of the following claims is claimed as property: 1. Aliphatic oligocarbonatopolols with a number average molecular weight (Mn) of 500 to 10000 g / mol, which are constituted by a polyol component, containing 1 to 99 mol% based on this polyol component of diols of formula characterized in that n is an integer from 1 to 50, m is an integer from 1 to 20, Ri, R are independently from each other a Ci to C2o alkyl moiety, which may be linear, cyclic or branched and optionally unsaturated, and (X) m is a group containing carbon with 1 to 20 C atoms, whose chain can also be interrupted with heteroatoms such as oxygen, sulfur or nitrogen and additionally as a constituent has at least one additional aliphatic polyol, totaling the sum of the amounts of the diol of formula (I) and of the other polyols contained in 100% by moles.
- 2. Process for the preparation of aliphatic oligocarbonatopolioles according to claim 1, which is based on a polyol component containing from 1 to 99 mol% based on this polyol component of diols of formula (I) characterized in that n is an integer from 1 to 50, m is an integer from 1 to 20, (X) m is a group containing carbon with 1 to 20 C atoms, whose chain may also be interrupted with heteroatoms such as oxygen , sulfur or nitrogen and Ri, R2 are independently of one another an alkyl moiety Ci to C20, which may be linear, cyclic or branched and optionally unsaturated, and additionally as a constituent has at least one other aliphatic polyol, totaling the sum of the amounts of the diol of formula (I) and of the other polyols contained 100% by mole.
- 3. Method according to claim 2, characterized in that in formula (I) (X) m is an alkyl group n is an integer from 1 to 10, m is an integer from 1 to 5 and R-_ = R2 = methyl. . Process according to claim 2 or 3, characterized in that the diols of formula (I) are contained in the aliphatic polyol component in 1 to 75% in moles and the other aliphatic polyols in 25 to 99% in moles. Method according to one of claims 2 to 4, characterized in that the other aliphatic polyols are saturated aliphatic or cycloaliphatic polyols, which optionally are branched and have primary or secondary attached OH groups and an OH = 2 functionality. Process according to one of claims 2 to 5, characterized in that the preparation is carried out by transesterification of organic carbonates. 7. Method according to claim 6, characterized in that a catalyst is used. 8. Process according to claim 6 or 7, characterized in that diphenyl carbonate (DPC), dimethyl carbonate (DMC), diethyl carbonate (DEC) and / or ethylene carbonate are used as the organic carbonate. 9. Use of the aliphatic oligocarbonatopolols according to claim 1, in the preparation of coatings, adhesives and sealing substances as well as polyurethane prepolymers.
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